(3aR,3bS,5S,7aS,7bS,8S,9aS,10R,11S,12aS,12bS,12cR)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,7a,9a-tetramethyl-8-triethylsilanyloxy-10-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-11-ol | 871247-73-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3aR,3bS,5S,7aS,7bS,8S,9aS,10R,11S,12aS,12bS,12cR)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,7a,9a-tetramethyl-8-triethylsilanyloxy-10-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-11-ol
• CAS: 871247-73-3
• 化学式: C₄₃H₈₀O₅Si₂
• 分子量: 733.276
• InChiKey: BURSOBCRTNXKLJ-FZKUUPQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.23
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3aR,3bS,5S,7aS,7bS,8S,9aS,10R,11S,12aS,12bS,12cR)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,7a,9a-tetramethyl-8-triethylsilanyloxy-10-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-11-ol 在 吡啶 、 4-二甲氨基吡啶 、 1,2-乙二硫醇 、 (+)-10-camphorsulfonic acid 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 [(3S,5S,6R,7R,8S,9S,10S,11S,13S,14S,16S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-6,7-dihydroxy-10,13-dimethyl-11-triethylsilyloxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl] acetate
  参考文献：
  名称：

  The Synthesis and Preliminary Biological Evaluation of a Novel Steroid with Neurotrophic Activity:  NGA0187

  摘要：

  A full account of the total synthesis of neurotrophic compound NGA0187 is provided. A key feature of the synthesis involved the direct selective oxidation of 6 alpha,7 beta-diol to install the unusual 6,7-ketol moiety and stereoselective conjugate addition of vinyl cuprate to enone. A preliminary evaluation of its ability to stimulate the neurite outgrowth was also evaluated with PC12 cell.

  DOI：

  10.1021/jo051556d
• 作为产物：
  描述：

  (3S,5S,6R,7R,8S,9S,10S,11S,13S,14S)-10,13-dimethyl-3,11-bis(triethylsilyloxy)spiro[1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-6,7-diol 在 2,6-二甲基吡啶 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 selenium(IV) oxide 、 potassium tert-butylate 、 叔丁基锂 、 copper(l) cyanide 、 戴斯-马丁氧化剂 、 溶剂黄146 、 (+)-10-camphorsulfonic acid 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 21.5h， 生成 (3aR,3bS,5S,7aS,7bS,8S,9aS,10R,11S,12aS,12bS,12cR)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,7a,9a-tetramethyl-8-triethylsilanyloxy-10-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-11-ol
  参考文献：
  名称：

  The Synthesis and Preliminary Biological Evaluation of a Novel Steroid with Neurotrophic Activity:  NGA0187

  摘要：

  A full account of the total synthesis of neurotrophic compound NGA0187 is provided. A key feature of the synthesis involved the direct selective oxidation of 6 alpha,7 beta-diol to install the unusual 6,7-ketol moiety and stereoselective conjugate addition of vinyl cuprate to enone. A preliminary evaluation of its ability to stimulate the neurite outgrowth was also evaluated with PC12 cell.

  DOI：

  10.1021/jo051556d